2-Picolylamine

2-Picolylamine
Names
	Other names 2-aminomethylpyridine
Identifiers
CAS Number	3731-51-9;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:81387;
ChEMBL	ChEMBL32189;
ChemSpider	18383;
EC Number	223-090-5;
KEGG	C17926;
PubChem CID	19509;
	InChI InChI=1S/C6H8N2/c7-5-6-3-1-2-4-8-6/h1-4H,5,7H2 Key: WOXFMYVTSLAQMO-UHFFFAOYSA-N;
	SMILES C1=CC=NC(=C1)CN;
Properties
Chemical formula	C6H8N2
Molar mass	108.144 g·mol−1
Density	1.105 g/cm3
Melting point	−20 °C (−4 °F; 253 K)
Boiling point	203 °C (397 °F; 476 K)
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H314, H319, H335
GHS precautionary statements	P260, P261, P264, P271, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P337+313, P363, P403+233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

2-Picolylamine is an organic compound with the formula H₂NCH₂C₅H₄N. A colorless liquid, it is a common bidentate ligand and a precursor to more complex multidentate ligands. It is usually prepared by hydrogenation of 2-cyanopyridine. One such complex is Baratta's catalyst RuCl₂(PPh₃)₂(ampy) (ampy = 2-picolylamine) for transfer hydrogenation.[1] Salts of the complex [Fe(pyCH₂NH₂)₃]²⁺ exhibit spin crossover behavior, whereby the complex switches from high to low spin configurations, depending on the temperature.[2]

Safety

The LD50 is low, being 750 mg/kg (oral, quail).[3]

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References

Chelucci, Giorgio; Baldino, Salvatore; Baratta, Walter (2015). "Ruthenium and Osmium Complexes Containing 2-(aminomethyl)pyridine (Ampy)-Based Ligands in Catalysis". Coordination Chemistry Reviews. 300: 29–85. doi:10.1016/j.ccr.2015.04.007.
Gütlich, P. (2001). "Photoswitchable Coordination Compounds". Coordination Chemistry Reviews. 219-221: 839–879. doi:10.1016/S0010-8545(01)00381-2.
Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399.

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[1] Chelucci, Giorgio; Baldino, Salvatore; Baratta, Walter (2015). "Ruthenium and Osmium Complexes Containing 2-(aminomethyl)pyridine (Ampy)-Based Ligands in Catalysis". Coordination Chemistry Reviews. 300: 29–85. doi:10.1016/j.ccr.2015.04.007.

[2] Gütlich, P. (2001). "Photoswitchable Coordination Compounds". Coordination Chemistry Reviews. 219-221: 839–879. doi:10.1016/S0010-8545(01)00381-2.

[Ullmann-3] Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399.